Guest house holiday rentals in Long Island Sound
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Top-rated guest house rentals in Long Island Sound
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for guest house rentals in Long Island Sound
Family-friendly guest house rentals
Guest house in Oyster Bay
4.96 out of 5 average rating, 179 reviewsGORGEOUS & SERENE in Oyster Bay - LI/NY
15–22 Nov
Guest house in South Salem
4.93 out of 5 average rating, 220 reviews1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
13–20 Feb
Guest house in Charlestown
4.88 out of 5 average rating, 269 reviewsCozy All Season Cabin Near Beach at Rockbriar Farm
13–20 Feb
Guest house in Shelter Island
4.97 out of 5 average rating, 105 reviewsWaterfront carriage house studio
29 Aug – 5 Sep
Guest house in Groton
4.94 out of 5 average rating, 386 reviewsQuiet studio with sleeping loft and deck
26 Oct – 2 Nov
Guest house in Jamesport
4.97 out of 5 average rating, 107 reviewsWalk to Beautiful Beach in Heart of Wine Country
15–22 Jan
Guest house in New Paltz
4.99 out of 5 average rating, 390 reviewsRidge View Walk-Up | Your GUNKS Home
12–19 Jun
Guest house in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
2–9 Mar
Guest house rentals with a patio
Guest house in Brewster
4.94 out of 5 average rating, 100 reviewsSherwood Barn - close to ski mountain
22–29 Oct
Guest house in Gardiner
4.99 out of 5 average rating, 137 reviewsRed Barn Retreat - Shawangunk Mountains Getaway
28 May – 4 Jun
Guest house in Montgomery
4.93 out of 5 average rating, 122 reviewsLuxury mins from angry orchard and city winery
3–10 Dec
Guest house in Shirley
4.97 out of 5 average rating, 36 reviewsLa little house J place
18–25 Jan
Guest house in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
25 Sep – 2 Oct
Guest house in North Castle
4.98 out of 5 average rating, 44 reviewsMagical 1700's 1 bedroom cottage
30 Aug – 6 Sep
Guest house in Weston
4.96 out of 5 average rating, 26 reviewsNature Lovers Guesthouse
4–11 Sep
Guest house in Southbury
4.96 out of 5 average rating, 52 reviewsThe Nest. Large studio in the Woods.
2–9 Mar
Guest house rentals with a washing machine and dryer
Guest house in Brewster
5.0 out of 5 average rating, 291 reviewsThe Cottage by the Lake: Hudson Valley Indulgence
1–8 Aug
Guest house in Stonington
4.97 out of 5 average rating, 223 reviewsTrue Artist Loft, 5 minutes to downtown Mystic
16–23 Oct
Guest house in Stonington
4.99 out of 5 average rating, 188 reviewsSuper Adorable Cottage + Fire pit + King Bed!
26 Oct – 2 Nov
Guest house in Bedford Hills
4.91 out of 5 average rating, 112 reviewsBarrett's Sanctuary
21–28 Sep
Guest house in Mamaroneck
4.95 out of 5 average rating, 128 reviewsYour Modern Guest Wing Near NYC
23–30 Jun
Guest house in Southold
4.95 out of 5 average rating, 41 reviewsSouthold- Adorable 1 Bedroom Cottage
9–16 May
Guest house in Madison
5.0 out of 5 average rating, 59 reviewsThe Barn by the Sound
17–24 Nov
Guest house in South Salem
5.0 out of 5 average rating, 66 reviewsNewly renovated guesthouse with a patio
8–15 Jul
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